1. Field of the Invention
The present invention relates to a method for producing optically active glycol derivatives by biochemical resolution which comprises contacting a racemic ester of the general formula 1 ##STR4## (wherein R.sub.1 is an aliphatic hydrocarbon group of 1 to 16 carbon atoms, R.sub.2 is an aliphatic hydrocarbon group of 1 to 8 carbon atoms, and R.sub.3 is an aromatic hydrocarbon group such as phenyl, tolyl or naphthyl) with a microorganism- or animal organ-derived enzyme having stereoselective hydrolytic activity to asymmetrically hydrolyze said racemic ester of general formula 1 to produce an optically active alcohol of general formula 2* ##STR5## (wherein R.sub.1 and R.sub.3 have the same meanings as defined above) and an unreacted ester of the general formula 1* ##STR6## (wherein R.sub.1, R.sub.2 and R.sub.3 have the same meanings as defined hereinbefore) and, then, isolating the respective optically active compounds.
In another aspect, the present invention further comprises a method for producing an optically active glycol derivative which comprises hydrolyzing said ester of general formula 1* to give an optically active glycol derivative which is antipodal to the alcohol of general formula 2* and, then, isolating the same optically active glycol derivative.
2. Description of the Prior Art
The optically active glycol derivatives mentioned above are versatile starting materials for the production of various optically active pharmaceutical products, agricultural chemicals and so on.
Taking 1-p-tosyloxy-2-propanol ##STR7## which corresponds to R.sub.1 =methyl and R.sub.3 =tolyl, as an example, it can be easily converted to propylene oxide ##STR8## and this optically active propylene oxide can be further converted to various physiologically active substances [Uchimoto et al: Tetrahedron Letters, 3641 (1977), synthesis of (R)-recifeiolide from (R)-propylene oxide; and W. Seidel & D. Seebach: Tetrahedron Letters 23, 159 (1982), synthesis of grahamimycin A.sub.1 from (R)-propylene oxide]
Further, in the case of 1-p-tosyloxy-2-tridecanol ##STR9## which corresponds to R.sub.1 =undecyl (C.sub.11 H.sub.23) and R.sub.3 =tolyl, it can be easily converted to 1,2-epoxytridecane ##STR10## which, in turn, can be converted to .delta.-n-hexadecalactone ##STR11## an insect pheromone [J. L. Coke & A. B. Richon: Journal of Organic Chemistry 22, 3516 (1976); and Fujisawa et al: Tetrahedron Letters 26, 771 (1985)].
These optically active glycol derivatives can be respectively synthesized, for example, by means of an optically active acid after conversion to an amine or by esterifying lactic acid or 3-hydroxybutyric acid from a fermentation process, reducing the ester with a reducing agent such as lithium aluminum hydride to give 1,2-propanediol or 1,2-butanediol and introducing a sulfonic acid group into the 1-position [B. Seuring: Helvetica Chimica Acta 60, 1175 (1977)].
However, these methods are disadvantageous in that complicated procedures are involved or costly reagents must be employed, and are not suitable for commercial scale production. Therefore, the establishment of an expedient method for production of such optically active compounds has been earnestly awaited.